Hexanoyl chloride → HCID 57841362, compound

HRID 733640Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][NH:18][C:19]3[CH:20]=[CH:21][C:22]4[C:27](=[O:28])[O:26][C:25]([CH3:30])([CH3:29])[O:24][C:23]=4[CH:31]=3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].[C:34](Cl)(=[O:40])[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:33]=[CH:32][C:16]([CH2:17][N:18]([C:19]3[CH:20]=[CH:21][C:22]4[C:27](=[O:28])[O:26][C:25]([CH3:29])([CH3:30])[O:24][C:23]=4[CH:31]=3)[C:34](=[O:40])[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39])=[CH:15][CH:14]=2)=[CH:9][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 67340Hexanoyl chloride

HCID 114192887-[4-(4-Butyl-phenylethynyl)-benzylamino]-2,2-dimethyl-benzo[1,3]dioxin-4-one

Product 1

HCID 57841362HCID 57841362, compound

Procedure

The titled compound was prepared following the procedure M using 7-({4-[(4-butylphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one and hexanoyl chloride as all orange oil (69%). 1H NMR (CDCl3, 300 MHz) δ 7.92 (d, J=8.3 Hz, 1H), 7.41 (m, 4H), 7.14 (m, 4H), 6.78 (d, J=8.3 Hz, 1H), 6.59 (s, 1H), 4.89 (s, 2H), 2.60 (t, J=7.7 Hz, 2H), 2.14 (t, J=7.3 Hz, 2H), 1.71 (s, 6H), 1.66-1.51 (m, 4H), 1.43-1.12 (m, 8H), 0.91 (t, J=7.3 Hz, 3H). 0.84 (t, J=6.7 Hz, 3H). M+ (ESI): 538.2. HPLC, Rt: 6.34 min (Purity: 99.4%).

Sources & evidence

ORD record: ord-9d7e12c76ea848a5819681efd674884e
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589232B2

Reaction notes

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